(2S,3S,4S,5S)-1,2-O-isopropylidene-3,6-anhydro-4-O-benzyl-5-azido-5-deoxy-D-glucitol

Base Information

Chemical Name:(2S,3S,4S,5S)-1,2-O-isopropylidene-3,6-anhydro-4-O-benzyl-5-azido-5-deoxy-D-glucitol
CAS No.:936946-79-1
Molecular Formula:C₁₆H₂₁N₃O₄
Molecular Weight:319.36
Hs Code.:

Synonyms:(2S,3S,4S,5S)-1,2-O-isopropylidene-3,6-anhydro-4-O-benzyl-5-azido-5-deoxy-D-glucitol

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Chemical Property of (2S,3S,4S,5S)-1,2-O-isopropylidene-3,6-anhydro-4-O-benzyl-5-azido-5-deoxy-D-glucitol

Chemical Property:

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Technology Process of (2S,3S,4S,5S)-1,2-O-isopropylidene-3,6-anhydro-4-O-benzyl-5-azido-5-deoxy-D-glucitol

There total 6 articles about (2S,3S,4S,5S)-1,2-O-isopropylidene-3,6-anhydro-4-O-benzyl-5-azido-5-deoxy-D-glucitol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 936946-80-4
(2S,3S,4S,5R)-1,2-O-isopropylidine-3,6-anhydro-4-O-benzyl-5-O-methane-sulfonyl-D-galactitol

: 936946-79-1
(2S,3S,4S,5S)-1,2-O-isopropylidene-3,6-anhydro-4-O-benzyl-5-azido-5-deoxy-D-glucitol

Guidance literature:: With sodium azide; tetrabutyl-ammonium chloride; In N,N-dimethyl-formamide; at 120 ℃; for 72h;
DOI:10.1016/j.tetasy.2007.02.021

Reference yield:

: 80040-79-5
3,4,6-tri-O-benzyl-D-galactal

: 936946-79-1
(2S,3S,4S,5S)-1,2-O-isopropylidene-3,6-anhydro-4-O-benzyl-5-azido-5-deoxy-D-glucitol

Guidance literature:: Multi-step reaction with 6 steps

1: aq. H₂SO₄ / HgSO₄ / dioxane / 8 h / 0 - 20 °C

2: NaBH₄; CeCl₃*7H₂O / ethanol / 3 h / 0 - 20 °C

3: L-(+)-diethyl tartrate; t-BuOOH / Ti(O-i-Pr)4 / CH₂Cl₂ / 2.5 h / -25 - 0 °C

4: citric acid / 2 h

5: triethylamine / CH₂Cl₂ / 1.5 h / 0 - 20 °C

6: 269 mg / NaN₃; Bu₄NCl / dimethylformamide / 72 h / 120 °C

With tert.-butylhydroperoxide; sodium tetrahydroborate; sodium azide; cerium(III) chloride; diethyl (2R,3R)-tartrate; sulfuric acid; tetrabutyl-ammonium chloride; triethylamine; citric acid; titanium(IV) isopropylate; mercury(II) sulfate; In 1,4-dioxane; ethanol; dichloromethane; N,N-dimethyl-formamide; 1: Perlin hydrolysis / 3: Sharpless asymmetric epoxidation;
DOI:10.1016/j.tetasy.2007.02.021

Reference yield:

: 137410-20-9
(2E)-4,6-di-O-benzyl-2,3-dideoxy-aldehydo-D-threo-hex-2-enose

: 936946-79-1
(2S,3S,4S,5S)-1,2-O-isopropylidene-3,6-anhydro-4-O-benzyl-5-azido-5-deoxy-D-glucitol

Guidance literature:: Multi-step reaction with 5 steps

1: NaBH₄; CeCl₃*7H₂O / ethanol / 3 h / 0 - 20 °C

2: L-(+)-diethyl tartrate; t-BuOOH / Ti(O-i-Pr)4 / CH₂Cl₂ / 2.5 h / -25 - 0 °C

3: citric acid / 2 h

4: triethylamine / CH₂Cl₂ / 1.5 h / 0 - 20 °C

5: 269 mg / NaN₃; Bu₄NCl / dimethylformamide / 72 h / 120 °C

With tert.-butylhydroperoxide; sodium tetrahydroborate; sodium azide; cerium(III) chloride; diethyl (2R,3R)-tartrate; tetrabutyl-ammonium chloride; triethylamine; citric acid; titanium(IV) isopropylate; In ethanol; dichloromethane; N,N-dimethyl-formamide; 2: Sharpless asymmetric epoxidation;
DOI:10.1016/j.tetasy.2007.02.021